Poly[[μ4-naphthalene-1,4-dicarboxyl­ato-κ4O:O′:O′′:O′′′-μ2-naphthalene-1,4-dicarboxyl­ato-κ4O,O′:O′′,O′′′-bis­(2-phenyl-1H-1,3,7,8-tetra­azacyclopenta­[l]phenanthrene-κ2N7,N8)dimanganese(II)] N,N-dimethyl­formamide solvate]

Li, H.-D.; Liu, Y.; Xu, M.-L.; Ng, S.W.

doi:10.1107/S1600536808010787

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m704-m705

doi:10.1107/S1600536808010787

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Poly[[μ₄-naphthalene-1,4-dicarboxylato-κ⁴O:O′:O′′:O′′′-μ₂-naphthalene-1,4-dicarboxylato-κ⁴O,O′:O′′,O′′′-bis(2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene-κ²N⁷,N⁸)dimanganese(II)] N,N-dimethylformamide solvate]

Heng-Da Li,^a Yang Liu,^a Mao-Liang Xu ^b and Seik Weng Ng ^c ^*

^aDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China, ^bXi'an Modern Chemistry Research Institute, Xi'an 710065, People's Republic of China, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 16 January 2008; accepted 18 April 2008; online 23 April 2008)

One of the two 1,4-dicarboxylate dianions in the title compound, [Mn₂(C₁₂H₆O₄)₂(C₁₉H₁₂N₄)₂]·C₃H₇NO, uses its two carboxylate groups to chelate two N-heterocycle-chelated Mn atoms; the other 1,4-dicarboxylate dianion binds to four such metal centers. The octahedrally coordinated Mn atoms are linked through the two dianions into a layer motif; the dimethylformamide molecules occupy the spaces between adjacent layers. Ten C atoms and attached H atoms of one dianion are disordered equally over two positions.

Related literature

There are several studies of 2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene-chelated metal compounds; for the structures of the manganese dicarboxylate adducts, see: Che (2006 ); Che & Liu (2006 ); Wang et al. (2006 ); Zhang et al. (2006 ).

Experimental

Crystal data

[Mn₂(C₁₂H₆O₄)₂(C₁₉H₁₂N₄)₂]·C₃H₇NO
M_r = 1203.96
Triclinic, $[P \overline 1]$
a = 9.240 (2) Å
b = 14.852 (5) Å
c = 21.921 (5) Å
α = 105.72 (1)°
β = 100.48 (1)°
γ = 101.67 (1)°
V = 2745.0 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 295 (2) K
0.26 × 0.16 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.760, T_max = 0.940
21501 measured reflections
9443 independent reflections
4800 reflections with I > 2σ(I)
R_int = 0.084

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.262
S = 1.06
9443 reflections
810 parameters
158 restraints
H-atom parameters constrained
Δρ_max = 1.74 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—O1ⁱ	2.115 (5)
Mn1—O4ⁱⁱ	2.105 (4)
Mn1—O5	2.431 (5)
Mn1—O6	2.171 (5)
Mn1—N1	2.232 (5)
Mn1—N4	2.259 (5)
Mn2—O2	2.107 (5)
Mn2—O3ⁱⁱⁱ	2.112 (5)
Mn2—O7	2.208 (5)
Mn2—O8	2.384 (5)
Mn2—N5	2.252 (6)
Mn2—N8	2.277 (5)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ) and OLEX (Dolomanov et al., 2003 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010787/rz2195sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010787/rz2195Isup2.hkl

checkCIF report

Comment top

There are several studies of metal complexes of 2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene. Among these are several manganese complexes, the manganese succinate (Zhang et al., 2006), manganese adipate (Wang et al., 2006), manganese isophthalate (Che & Liu, 2006) and manganese terephthalate (Che, 2006) adducts, all of which feature carboxylate-bridged chain motifs. The title naphthalene-1,4-dicarboxylate adduct adopts a layer motif instead.

One of the two 1,4-dicarboxylate dianions in Mn₂(C₁₉H₁₂N₄)₂(C₁₂H₆O₄)₂^.DMF uses its two carboxyl –CO₂ groups to chelate to two N-heterocycle-chelated manganese atoms; the other 1,4-dicarboxylate dianion binds to four such metal centers. The octahedrally coordinated manganese atoms are linked through the two dianions into a layer motif; the DMF molecules occupy the spaces between adjacent layers.

Related literature top

There are several studies of 2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene-chelated metal compounds; for the structures of the manganese dicarboxylate adducts, see: Che (2006); Che & Liu (2006); Wang et al. (2006); Zhang et al. (2006).

Experimental top

Manganese dichloride dihydrate (0.1 mmol), naphthalene-1,4-dicarboxylic acid (0.1 mmol), 2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene (0.1 mmol), water (8 ml) and DMF (4 ml) were heated in a 23 ml, Teflon-lined, stainless-steel Parr bomb at 408 K for 2 days. Crystals were obtained in 40% yield.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

	Fig. 1. Thermal ellipsoid plot of Mn₂(C₁₉H₁₂N₄)₂(C₁₂H₆O₄)₂^.DMF; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. The disorder in one of the naphthalene-1,4-dicarboxylate dianions is not shown. Symmetry codes are given in Table 1.
	Fig. 2. Layer structure of the manganese-naphthalene-1,4-dicarboxylate network as illustrated by OLEX (Dolomanov et al., 2003).

Poly[[µ₄-naphthalene-1,4-dicarboxylato- κ⁴O:O':O'':O'''- µ₂-naphthalene-1,4-dicarboxylato- κ⁴O,O':O'',O'''- bis(2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene- κ²N⁷,N⁸)dimanganese(II)] N,N-dimethylformamide solvate] top

Crystal data top

[Mn₂(C₁₂H₆O₄)₂(C₁₉H₁₂N₄)₂]·C₃H₇NO	Z = 2
M_r = 1203.96	F(000) = 1236
Triclinic, P1	D_x = 1.457 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.240 (2) Å	Cell parameters from 15789 reflections
b = 14.852 (5) Å	θ = 3.0–27.5°
c = 21.921 (5) Å	µ = 0.53 mm⁻¹
α = 105.72 (1)°	T = 295 K
β = 100.48 (1)°	Block, colorless
γ = 101.67 (1)°	0.26 × 0.16 × 0.12 mm
V = 2745.0 (13) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	9443 independent reflections
Radiation source: fine-focus sealed tube	4800 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.084
Detector resolution: 10 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scans	h = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→17
T_min = 0.760, T_max = 0.940	l = −26→26
21501 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.262	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1308P)² + 1.0767P] where P = (F_o² + 2F_c²)/3
9443 reflections	(Δ/σ)_max = 0.001
810 parameters	Δρ_max = 1.74 e Å⁻³
158 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Mn₂(C₁₂H₆O₄)₂(C₁₉H₁₂N₄)₂]·C₃H₇NO	γ = 101.67 (1)°
M_r = 1203.96	V = 2745.0 (13) Å³
Triclinic, P1	Z = 2
a = 9.240 (2) Å	Mo Kα radiation
b = 14.852 (5) Å	µ = 0.53 mm⁻¹
c = 21.921 (5) Å	T = 295 K
α = 105.72 (1)°	0.26 × 0.16 × 0.12 mm
β = 100.48 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	9443 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4800 reflections with I > 2σ(I)
T_min = 0.760, T_max = 0.940	R_int = 0.084
21501 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	158 restraints
wR(F²) = 0.262	H-atom parameters constrained
S = 1.06	Δρ_max = 1.74 e Å⁻³
9443 reflections	Δρ_min = −0.48 e Å⁻³
810 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mn1	0.80675 (10)	0.75810 (7)	0.69248 (5)	0.0344 (3)
Mn2	1.06512 (11)	0.08617 (8)	0.75021 (6)	0.0431 (3)
O1	0.8244 (5)	−0.1078 (3)	0.7625 (2)	0.0484 (13)
O2	0.8416 (5)	0.0418 (4)	0.7602 (3)	0.0721 (19)
O3	0.0485 (5)	−0.0465 (4)	0.6792 (3)	0.0523 (14)
O4	0.0263 (5)	−0.1993 (4)	0.6783 (3)	0.0539 (14)
O5	0.8422 (5)	0.5979 (3)	0.6470 (2)	0.0394 (11)
O6	0.8715 (5)	0.6725 (4)	0.7537 (2)	0.0464 (13)
O7	1.0143 (5)	0.1880 (4)	0.6976 (3)	0.0500 (13)
O8	1.0396 (5)	0.2427 (4)	0.8038 (2)	0.0445 (12)
N1	0.6616 (5)	0.7650 (4)	0.6015 (3)	0.0358 (13)
N2	0.1203 (6)	0.6871 (5)	0.4819 (3)	0.0418 (15)
N3	0.0391 (6)	0.6310 (4)	0.5578 (3)	0.0372 (14)
H3N	−0.0221	0.6062	0.5778	0.045*
N4	0.5621 (6)	0.6932 (4)	0.6907 (3)	0.0335 (13)
N5	1.2081 (6)	0.0765 (4)	0.8419 (3)	0.0433 (15)
N6	1.7453 (6)	0.1593 (5)	0.9659 (3)	0.0479 (16)
N7	1.8308 (6)	0.2076 (4)	0.8873 (3)	0.0439 (15)
H7N	1.8936	0.2302	0.8671	0.053*
N8	1.3130 (6)	0.1489 (4)	0.7526 (3)	0.0427 (15)
C1	0.5938 (5)	−0.0627 (9)	0.7341 (5)	0.027 (8)	0.50
C2	0.5072 (7)	−0.1025 (11)	0.7707 (5)	0.029 (6)	0.50
H2	0.5551	−0.1156	0.8072	0.035*	0.50
C3	0.3489 (7)	−0.1228 (11)	0.7526 (5)	0.037 (5)	0.50
H3	0.2910	−0.1494	0.7771	0.045*	0.50
C4	0.2773 (5)	−0.1033 (10)	0.6980 (5)	0.048 (8)	0.50
C5	0.3640 (5)	−0.0635 (7)	0.6615 (4)	0.048 (10)	0.50
C6	0.5223 (5)	−0.0432 (7)	0.6795 (4)	0.034 (10)	0.50
C7	0.6089 (7)	−0.0034 (8)	0.6429 (5)	0.054 (4)	0.50
H7	0.7148	0.0102	0.6550	0.064*	0.50
C8	0.5373 (11)	0.0161 (8)	0.5883 (4)	0.071 (5)	0.50
H8	0.5953	0.0428	0.5639	0.085*	0.50
C9	0.3791 (11)	−0.0041 (8)	0.5703 (4)	0.067 (5)	0.50
H9	0.3312	0.0089	0.5338	0.081*	0.50
C10	0.2924 (8)	−0.0439 (9)	0.6069 (4)	0.063 (5)	0.50
H10	0.1865	−0.0575	0.5948	0.076*	0.50
C1'	0.5934 (5)	−0.0562 (9)	0.7394 (4)	0.047 (11)	0.50
C2'	0.5185 (7)	−0.0413 (10)	0.6835 (5)	0.048 (13)	0.50
H2'	0.5741	−0.0190	0.6567	0.058*	0.50
C3'	0.3604 (7)	−0.0597 (9)	0.6676 (4)	0.029 (8)	0.50
H3'	0.3102	−0.0497	0.6301	0.035*	0.50
C4'	0.2772 (5)	−0.0931 (8)	0.7076 (4)	0.021 (5)	0.50
C5'	0.3521 (5)	−0.1080 (5)	0.7635 (3)	0.028 (5)	0.50
C6'	0.5103 (5)	−0.0895 (6)	0.7794 (3)	0.040 (8)	0.50
C7'	0.5852 (6)	−0.1045 (7)	0.8353 (4)	0.039 (3)	0.50
H7'	0.6910	−0.0921	0.8460	0.047*	0.50
C8'	0.5020 (9)	−0.1378 (6)	0.8753 (3)	0.044 (4)	0.50
H8'	0.5522	−0.1478	0.9128	0.053*	0.50
C9'	0.3439 (9)	−0.1562 (6)	0.8594 (4)	0.046 (4)	0.50
H9'	0.2883	−0.1786	0.8862	0.055*	0.50
C10'	0.2690 (6)	−0.1413 (6)	0.8035 (4)	0.042 (3)	0.50
H10'	0.1632	−0.1537	0.7929	0.051*	0.50
C11	0.7665 (7)	−0.0412 (5)	0.7541 (4)	0.0456 (19)
C12	0.1025 (8)	−0.1168 (6)	0.6854 (3)	0.0422 (18)
C13	0.8782 (7)	0.6019 (5)	0.7074 (4)	0.0394 (17)
C14	0.9218 (7)	0.5171 (5)	0.7226 (3)	0.0370 (16)
C15	1.0253 (7)	0.5249 (5)	0.7819 (3)	0.0346 (16)
C16	1.0953 (8)	0.6157 (5)	0.8332 (4)	0.0485 (19)
H16	1.0697	0.6716	0.8290	0.058*
C17	1.1988 (9)	0.6212 (6)	0.8881 (4)	0.056 (2)
H17	1.2416	0.6804	0.9212	0.067*
C18	1.2410 (9)	0.5380 (7)	0.8948 (4)	0.063 (2)
H18	1.3150	0.5432	0.9315	0.075*
C19	1.1752 (8)	0.4502 (6)	0.8485 (4)	0.0492 (19)
H19	1.2030	0.3958	0.8545	0.059*
C20	1.0646 (7)	0.4397 (5)	0.7909 (3)	0.0369 (16)
C21	0.9922 (7)	0.3487 (5)	0.7412 (3)	0.0349 (16)
C22	0.8966 (8)	0.3436 (5)	0.6850 (4)	0.0407 (17)
H22	0.8517	0.2838	0.6527	0.049*
C23	0.8646 (7)	0.4275 (5)	0.6751 (3)	0.0388 (17)
H23	0.8027	0.4226	0.6352	0.047*
C24	1.0185 (7)	0.2543 (5)	0.7487 (4)	0.0402 (17)
C25	0.7115 (7)	0.8015 (5)	0.5574 (4)	0.0444 (18)
H25	0.8161	0.8266	0.5646	0.053*
C26	0.6146 (8)	0.8038 (6)	0.5007 (4)	0.052 (2)
H26	0.6547	0.8283	0.4707	0.063*
C27	0.4607 (8)	0.7695 (6)	0.4904 (3)	0.0472 (19)
H27	0.3947	0.7705	0.4532	0.057*
C28	0.4023 (7)	0.7326 (5)	0.5366 (3)	0.0340 (15)
C29	0.5081 (7)	0.7313 (5)	0.5913 (3)	0.0304 (14)
C30	0.2444 (7)	0.6954 (5)	0.5310 (3)	0.0360 (16)
C31	−0.0010 (7)	0.6479 (5)	0.4995 (3)	0.0404 (17)
C32	−0.1577 (7)	0.6204 (5)	0.4597 (3)	0.0407 (17)
C33	−0.1849 (8)	0.6449 (6)	0.4017 (4)	0.054 (2)
H33	−0.1045	0.6802	0.3906	0.065*
C34	−0.3294 (9)	0.6169 (7)	0.3616 (4)	0.062 (2)
H34	−0.3451	0.6322	0.3229	0.074*
C35	−0.4512 (8)	0.5666 (6)	0.3772 (4)	0.057 (2)
H35	−0.5489	0.5482	0.3498	0.068*
C36	−0.4247 (8)	0.5435 (6)	0.4359 (4)	0.058 (2)
H36	−0.5062	0.5104	0.4477	0.070*
C37	−0.2806 (7)	0.5693 (6)	0.4757 (4)	0.0454 (18)
H37	−0.2649	0.5525	0.5138	0.055*
C38	0.1968 (6)	0.6614 (5)	0.5786 (3)	0.0330 (15)
C39	0.2984 (7)	0.6593 (5)	0.6347 (3)	0.0324 (15)
C40	0.4544 (7)	0.6934 (5)	0.6397 (3)	0.0344 (15)
C41	0.2561 (8)	0.6218 (5)	0.6840 (4)	0.0447 (18)
H41	0.1537	0.5966	0.6814	0.054*
C42	0.3656 (7)	0.6229 (6)	0.7346 (3)	0.0441 (18)
H42	0.3389	0.6003	0.7678	0.053*
C43	0.5183 (7)	0.6582 (5)	0.7367 (3)	0.0406 (17)
H43	0.5928	0.6574	0.7712	0.049*
C44	1.1542 (8)	0.0416 (6)	0.8854 (4)	0.059 (2)
H44	1.0494	0.0165	0.8777	0.070*
C45	1.2488 (10)	0.0416 (7)	0.9412 (4)	0.072 (3)
H45	1.2068	0.0186	0.9714	0.086*
C46	1.4035 (9)	0.0746 (7)	0.9535 (4)	0.064 (2)
H46	1.4675	0.0727	0.9909	0.076*
C47	1.4632 (7)	0.1115 (5)	0.9083 (4)	0.0427 (18)
C48	1.3611 (7)	0.1117 (5)	0.8531 (3)	0.0385 (17)
C49	1.6241 (7)	0.1468 (5)	0.9147 (4)	0.0435 (18)
C50	1.8678 (8)	0.1949 (5)	0.9482 (3)	0.0425 (18)
C51	2.0230 (8)	0.2242 (6)	0.9890 (4)	0.0481 (19)
C52	2.0480 (9)	0.2083 (7)	1.0480 (4)	0.067 (3)
H52	1.9674	0.1757	1.0606	0.081*
C53	2.1936 (11)	0.2406 (8)	1.0891 (4)	0.085 (3)
H53	2.2091	0.2319	1.1300	0.103*
C54	2.3144 (10)	0.2850 (8)	1.0708 (5)	0.079 (3)
H54	2.4119	0.3047	1.0985	0.095*
C55	2.2923 (9)	0.3005 (7)	1.0116 (5)	0.075 (3)
H55	2.3744	0.3301	0.9985	0.090*
C56	2.1443 (9)	0.2713 (7)	0.9708 (4)	0.063 (2)
H56	2.1278	0.2839	0.9311	0.075*
C57	1.6738 (7)	0.1767 (5)	0.8654 (3)	0.0386 (17)
C58	1.5753 (8)	0.1778 (5)	0.8082 (4)	0.0420 (17)
C59	1.4184 (7)	0.1474 (5)	0.8023 (3)	0.0336 (15)
C60	1.6205 (8)	0.2092 (6)	0.7593 (4)	0.055 (2)
H60	1.7237	0.2287	0.7609	0.066*
C61	1.5131 (9)	0.2115 (6)	0.7086 (4)	0.058 (2)
H61	1.5414	0.2336	0.6755	0.070*
C62	1.3589 (8)	0.1797 (6)	0.7075 (4)	0.053 (2)
H62	1.2856	0.1806	0.6726	0.064*
O9	2.5478 (19)	0.3811 (10)	0.9394 (7)	0.251 (7)
N9	2.6817 (9)	0.4487 (5)	0.8833 (4)	0.081 (2)
C63	2.5473 (15)	0.4057 (7)	0.8923 (7)	0.148 (6)
H63	2.4561	0.3956	0.8620	0.178*
C64	2.8345 (11)	0.4717 (9)	0.9235 (6)	0.120 (4)
H64A	2.8304	0.4595	0.9641	0.181*
H64B	2.8841	0.5388	0.9322	0.181*
H64C	2.8908	0.4320	0.9010	0.181*
C65	2.6539 (17)	0.4727 (9)	0.8232 (5)	0.136 (5)
H65A	2.5459	0.4589	0.8055	0.204*
H65B	2.6969	0.4346	0.7921	0.204*
H65C	2.7004	0.5404	0.8321	0.204*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0223 (5)	0.0271 (6)	0.0533 (7)	0.0068 (4)	0.0067 (5)	0.0140 (5)
Mn2	0.0265 (6)	0.0289 (7)	0.0766 (8)	0.0103 (5)	0.0118 (5)	0.0196 (6)
O1	0.033 (3)	0.033 (3)	0.070 (3)	0.012 (2)	0.003 (2)	0.006 (3)
O2	0.029 (3)	0.034 (3)	0.151 (6)	0.009 (3)	0.035 (3)	0.016 (4)
O3	0.035 (3)	0.038 (3)	0.083 (4)	0.016 (2)	0.008 (3)	0.019 (3)
O4	0.029 (3)	0.031 (3)	0.101 (4)	0.007 (2)	0.025 (3)	0.016 (3)
O5	0.037 (3)	0.040 (3)	0.046 (3)	0.011 (2)	0.008 (2)	0.024 (2)
O6	0.051 (3)	0.040 (3)	0.059 (3)	0.025 (3)	0.017 (3)	0.020 (3)
O7	0.052 (3)	0.033 (3)	0.066 (3)	0.020 (3)	0.009 (3)	0.016 (3)
O8	0.042 (3)	0.042 (3)	0.063 (3)	0.018 (2)	0.016 (3)	0.030 (3)
N1	0.026 (3)	0.035 (4)	0.044 (3)	0.005 (2)	0.009 (3)	0.012 (3)
N2	0.027 (3)	0.060 (4)	0.037 (3)	0.008 (3)	0.004 (3)	0.018 (3)
N3	0.023 (3)	0.048 (4)	0.040 (3)	0.007 (3)	0.007 (3)	0.017 (3)
N4	0.029 (3)	0.027 (3)	0.038 (3)	0.005 (2)	0.000 (3)	0.008 (3)
N5	0.032 (3)	0.031 (4)	0.066 (4)	0.006 (3)	0.013 (3)	0.014 (3)
N6	0.040 (3)	0.051 (4)	0.053 (4)	0.013 (3)	0.013 (3)	0.014 (3)
N7	0.030 (3)	0.038 (4)	0.058 (4)	0.006 (3)	0.010 (3)	0.007 (3)
N8	0.028 (3)	0.038 (4)	0.065 (4)	0.009 (3)	0.011 (3)	0.021 (3)
C1	0.015 (10)	0.023 (10)	0.042 (10)	0.006 (7)	0.014 (7)	0.003 (6)
C2	0.026 (8)	0.017 (7)	0.036 (8)	0.004 (6)	0.000 (6)	0.002 (6)
C3	0.034 (9)	0.019 (7)	0.049 (8)	0.001 (6)	0.013 (7)	−0.003 (6)
C4	0.050 (11)	0.036 (11)	0.053 (9)	0.012 (8)	0.008 (8)	0.008 (7)
C5	0.045 (13)	0.047 (13)	0.055 (12)	0.013 (8)	0.013 (9)	0.020 (8)
C6	0.023 (12)	0.030 (13)	0.048 (12)	0.002 (7)	0.018 (8)	0.011 (7)
C7	0.053 (7)	0.049 (8)	0.061 (8)	0.011 (6)	0.018 (6)	0.021 (6)
C8	0.068 (8)	0.076 (9)	0.073 (8)	0.016 (7)	0.018 (7)	0.032 (7)
C9	0.059 (8)	0.076 (9)	0.075 (8)	0.027 (7)	0.019 (7)	0.030 (7)
C10	0.054 (8)	0.070 (9)	0.069 (8)	0.019 (7)	0.015 (7)	0.026 (7)
C1'	0.038 (13)	0.035 (13)	0.060 (13)	0.010 (9)	0.008 (9)	0.004 (8)
C2'	0.039 (15)	0.043 (15)	0.061 (14)	0.011 (9)	0.016 (9)	0.011 (8)
C3'	0.015 (9)	0.029 (10)	0.044 (10)	0.015 (7)	0.005 (7)	0.009 (6)
C4'	0.010 (7)	0.008 (7)	0.045 (8)	0.005 (5)	0.013 (6)	0.003 (5)
C5'	0.025 (8)	0.016 (8)	0.040 (8)	0.010 (6)	0.007 (6)	0.001 (6)
C6'	0.043 (10)	0.034 (10)	0.047 (10)	0.013 (7)	0.017 (8)	0.011 (7)
C7'	0.038 (6)	0.034 (7)	0.045 (7)	0.015 (5)	0.006 (5)	0.009 (5)
C8'	0.041 (6)	0.042 (7)	0.051 (7)	0.015 (6)	0.010 (6)	0.015 (6)
C9'	0.054 (7)	0.035 (7)	0.053 (7)	0.009 (6)	0.026 (6)	0.014 (6)
C10'	0.037 (6)	0.036 (7)	0.054 (7)	0.013 (5)	0.017 (6)	0.008 (6)
C11	0.026 (3)	0.029 (4)	0.075 (5)	0.004 (3)	0.012 (4)	0.009 (4)
C12	0.035 (4)	0.043 (5)	0.047 (4)	0.012 (4)	0.011 (3)	0.010 (4)
C13	0.028 (3)	0.036 (4)	0.063 (5)	0.008 (3)	0.019 (4)	0.024 (4)
C14	0.032 (4)	0.032 (4)	0.052 (4)	0.013 (3)	0.016 (3)	0.014 (3)
C15	0.028 (3)	0.040 (4)	0.040 (4)	0.010 (3)	0.011 (3)	0.015 (3)
C16	0.052 (5)	0.033 (5)	0.059 (5)	0.017 (4)	0.009 (4)	0.011 (4)
C17	0.062 (5)	0.042 (5)	0.052 (5)	0.014 (4)	0.004 (4)	0.004 (4)
C18	0.045 (5)	0.070 (7)	0.061 (5)	0.010 (5)	−0.008 (4)	0.020 (5)
C19	0.041 (4)	0.047 (5)	0.057 (5)	0.015 (4)	−0.004 (4)	0.021 (4)
C20	0.033 (3)	0.035 (4)	0.053 (4)	0.014 (3)	0.017 (3)	0.022 (4)
C21	0.030 (3)	0.030 (4)	0.048 (4)	0.009 (3)	0.013 (3)	0.015 (3)
C22	0.047 (4)	0.028 (4)	0.052 (4)	0.016 (3)	0.013 (4)	0.017 (3)
C23	0.029 (3)	0.050 (5)	0.040 (4)	0.012 (3)	0.008 (3)	0.018 (4)
C24	0.029 (4)	0.033 (4)	0.065 (5)	0.015 (3)	0.014 (4)	0.021 (4)
C25	0.027 (3)	0.050 (5)	0.060 (5)	0.008 (3)	0.019 (4)	0.019 (4)
C26	0.047 (4)	0.063 (6)	0.050 (5)	0.011 (4)	0.015 (4)	0.025 (4)
C27	0.049 (4)	0.060 (6)	0.039 (4)	0.018 (4)	0.013 (4)	0.023 (4)
C28	0.031 (3)	0.034 (4)	0.038 (4)	0.009 (3)	0.012 (3)	0.011 (3)
C29	0.025 (3)	0.028 (4)	0.036 (4)	0.004 (3)	0.005 (3)	0.011 (3)
C30	0.030 (4)	0.041 (4)	0.033 (4)	0.009 (3)	0.007 (3)	0.008 (3)
C31	0.029 (4)	0.048 (5)	0.041 (4)	0.013 (3)	0.008 (3)	0.010 (4)
C32	0.030 (4)	0.044 (5)	0.040 (4)	0.010 (3)	0.005 (3)	0.003 (3)
C33	0.042 (4)	0.064 (6)	0.057 (5)	0.011 (4)	0.011 (4)	0.023 (4)
C34	0.045 (5)	0.088 (7)	0.057 (5)	0.029 (5)	−0.001 (4)	0.030 (5)
C35	0.027 (4)	0.065 (6)	0.067 (5)	0.016 (4)	−0.001 (4)	0.010 (5)
C36	0.037 (4)	0.060 (6)	0.069 (6)	0.007 (4)	0.009 (4)	0.013 (5)
C37	0.034 (4)	0.049 (5)	0.052 (4)	0.009 (3)	0.007 (4)	0.019 (4)
C38	0.020 (3)	0.042 (4)	0.036 (4)	0.011 (3)	0.002 (3)	0.011 (3)
C39	0.026 (3)	0.027 (4)	0.043 (4)	0.007 (3)	0.007 (3)	0.009 (3)
C40	0.034 (4)	0.023 (4)	0.039 (4)	0.003 (3)	0.005 (3)	0.003 (3)
C41	0.033 (4)	0.048 (5)	0.060 (5)	0.007 (3)	0.019 (4)	0.026 (4)
C42	0.036 (4)	0.060 (5)	0.040 (4)	0.009 (4)	0.008 (3)	0.024 (4)
C43	0.027 (3)	0.051 (5)	0.042 (4)	0.007 (3)	0.002 (3)	0.019 (4)
C44	0.033 (4)	0.066 (6)	0.085 (6)	0.009 (4)	0.021 (5)	0.037 (5)
C45	0.056 (5)	0.102 (8)	0.075 (6)	0.018 (5)	0.032 (5)	0.049 (6)
C46	0.056 (5)	0.084 (7)	0.062 (5)	0.020 (5)	0.021 (5)	0.033 (5)
C47	0.032 (4)	0.041 (5)	0.056 (5)	0.007 (3)	0.017 (4)	0.015 (4)
C48	0.029 (3)	0.024 (4)	0.054 (4)	0.003 (3)	0.011 (3)	0.001 (3)
C49	0.033 (4)	0.042 (5)	0.051 (4)	0.016 (3)	0.005 (4)	0.007 (4)
C50	0.034 (4)	0.045 (5)	0.045 (4)	0.011 (3)	0.009 (3)	0.009 (4)
C51	0.038 (4)	0.053 (5)	0.045 (4)	0.012 (4)	0.006 (4)	0.006 (4)
C52	0.042 (5)	0.090 (8)	0.057 (5)	0.010 (5)	0.008 (4)	0.013 (5)
C53	0.066 (6)	0.131 (10)	0.034 (5)	0.015 (6)	−0.004 (5)	0.006 (5)
C54	0.037 (5)	0.105 (9)	0.070 (7)	0.008 (5)	−0.006 (5)	0.010 (6)
C55	0.039 (5)	0.084 (8)	0.084 (7)	0.002 (5)	0.013 (5)	0.011 (6)
C56	0.046 (5)	0.064 (6)	0.067 (6)	0.010 (4)	0.002 (4)	0.015 (5)
C57	0.030 (4)	0.031 (4)	0.053 (4)	0.012 (3)	0.012 (4)	0.008 (3)
C58	0.037 (4)	0.034 (4)	0.057 (5)	0.006 (3)	0.017 (4)	0.015 (4)
C59	0.032 (3)	0.023 (4)	0.044 (4)	0.008 (3)	0.006 (3)	0.009 (3)
C60	0.026 (4)	0.063 (6)	0.078 (6)	0.008 (4)	0.010 (4)	0.031 (5)
C61	0.047 (5)	0.056 (6)	0.082 (6)	0.007 (4)	0.019 (5)	0.041 (5)
C62	0.038 (4)	0.050 (5)	0.077 (6)	0.007 (4)	0.015 (4)	0.032 (5)
O9	0.266 (11)	0.249 (11)	0.242 (10)	0.055 (8)	0.089 (8)	0.080 (8)
N9	0.072 (5)	0.072 (5)	0.096 (5)	0.011 (4)	0.031 (4)	0.019 (4)
C63	0.159 (8)	0.143 (8)	0.145 (8)	0.046 (6)	0.043 (6)	0.044 (6)
C64	0.086 (9)	0.110 (11)	0.142 (11)	0.010 (8)	0.012 (8)	0.027 (9)
C65	0.180 (9)	0.124 (9)	0.122 (8)	0.042 (7)	0.061 (7)	0.052 (7)

Geometric parameters (Å, º) top

Mn1—O1ⁱ	2.115 (5)	C17—C18	1.406 (11)
Mn1—O4ⁱⁱ	2.105 (4)	C17—H17	0.9300
Mn1—O5	2.431 (5)	C18—C19	1.355 (11)
Mn1—O6	2.171 (5)	C18—H18	0.9300
Mn1—N1	2.232 (5)	C19—C20	1.421 (9)
Mn1—N4	2.259 (5)	C19—H19	0.9300
Mn2—O2	2.107 (5)	C20—C21	1.426 (9)
Mn2—O3ⁱⁱⁱ	2.112 (5)	C21—C22	1.351 (9)
Mn2—O7	2.208 (5)	C21—C24	1.516 (9)
Mn2—O8	2.384 (5)	C22—C23	1.400 (9)
Mn2—N5	2.252 (6)	C22—H22	0.9300
Mn2—N8	2.277 (5)	C23—H23	0.9300
O1—C11	1.255 (8)	C25—C26	1.407 (10)
O2—C11	1.246 (8)	C25—H25	0.9300
O3—C12	1.272 (8)	C26—C27	1.363 (9)
O4—C12	1.237 (8)	C26—H26	0.9300
O4—Mn1^iv	2.105 (4)	C27—C28	1.414 (9)
O5—C13	1.285 (8)	C27—H27	0.9300
O6—C13	1.268 (8)	C28—C29	1.410 (9)
O7—C24	1.264 (8)	C28—C30	1.421 (8)
O8—C24	1.252 (8)	C29—C40	1.445 (9)
N1—C25	1.335 (8)	C30—C38	1.378 (9)
N1—C29	1.360 (7)	C31—C32	1.460 (9)
N2—C31	1.325 (8)	C32—C37	1.389 (9)
N2—C30	1.381 (8)	C32—C33	1.408 (10)
N3—C31	1.370 (9)	C33—C34	1.371 (10)
N3—C38	1.384 (7)	C33—H33	0.9300
N3—H3N	0.8600	C34—C35	1.371 (11)
N4—C43	1.342 (8)	C34—H34	0.9300
N4—C40	1.357 (8)	C35—C36	1.411 (11)
N5—C44	1.327 (9)	C35—H35	0.9300
N5—C48	1.356 (8)	C36—C37	1.367 (10)
N6—C50	1.319 (8)	C36—H36	0.9300
N6—C49	1.375 (9)	C37—H37	0.9300
N7—C57	1.380 (8)	C38—C39	1.416 (9)
N7—C50	1.390 (9)	C39—C40	1.401 (8)
N7—H7N	0.8600	C39—C41	1.423 (9)
N8—C62	1.298 (9)	C41—C42	1.353 (9)
N8—C59	1.331 (8)	C41—H41	0.9300
C1—C2	1.3900	C42—C43	1.390 (9)
C1—C6	1.3900	C42—H42	0.9300
C1—C11	1.517 (8)	C43—H43	0.9300
C2—C3	1.3900	C44—C45	1.370 (11)
C2—H2	0.9300	C44—H44	0.9300
C3—C4	1.3900	C45—C46	1.365 (11)
C3—H3	0.9300	C45—H45	0.9300
C4—C5	1.3900	C46—C47	1.399 (10)
C4—C12	1.550 (8)	C46—H46	0.9300
C5—C6	1.3900	C47—C48	1.393 (10)
C5—C10	1.3900	C47—C49	1.441 (9)
C6—C7	1.3900	C48—C59	1.490 (9)
C7—C8	1.3900	C49—C57	1.391 (10)
C7—H7	0.9300	C50—C51	1.454 (10)
C8—C9	1.3900	C51—C52	1.365 (11)
C8—H8	0.9300	C51—C56	1.379 (11)
C9—C10	1.3900	C52—C53	1.384 (11)
C9—H9	0.9300	C52—H52	0.9300
C10—H10	0.9300	C53—C54	1.360 (13)
C1'—C2'	1.3900	C53—H53	0.9300
C1'—C6'	1.3900	C54—C55	1.365 (13)
C1'—C11	1.530 (8)	C54—H54	0.9300
C2'—C3'	1.3900	C55—C56	1.400 (11)
C2'—H2'	0.9300	C55—H55	0.9300
C3'—C4'	1.3900	C56—H56	0.9300
C3'—H3'	0.9300	C57—C58	1.415 (10)
C4'—C5'	1.3900	C58—C60	1.377 (10)
C4'—C12	1.535 (8)	C58—C59	1.399 (9)
C5'—C6'	1.3900	C60—C61	1.362 (11)
C5'—C10'	1.3900	C60—H60	0.9300
C6'—C7'	1.3900	C61—C62	1.401 (10)
C7'—C8'	1.3900	C61—H61	0.9300
C7'—H7'	0.9300	C62—H62	0.9300
C8'—C9'	1.3900	O9—C63	1.18 (2)
C8'—H8'	0.9300	N9—C63	1.351 (9)
C9'—C10'	1.3900	N9—C64	1.440 (8)
C9'—H9'	0.9300	N9—C65	1.449 (8)
C10'—H10'	0.9300	C63—H63	0.9300
C13—C14	1.499 (9)	C64—H64A	0.9600
C14—C23	1.378 (9)	C64—H64B	0.9600
C14—C15	1.427 (9)	C64—H64C	0.9600
C15—C16	1.437 (10)	C65—H65A	0.9600
C15—C20	1.438 (9)	C65—H65B	0.9600
C16—C17	1.366 (10)	C65—H65C	0.9600
C16—H16	0.9300

O4ⁱⁱ—Mn1—O1ⁱ	94.88 (19)	C20—C19—H19	119.3
O4ⁱⁱ—Mn1—O6	94.6 (2)	C19—C20—C21	123.1 (6)
O1ⁱ—Mn1—O6	102.2 (2)	C19—C20—C15	118.5 (7)
O4ⁱⁱ—Mn1—N1	101.0 (2)	C21—C20—C15	118.3 (6)
O1ⁱ—Mn1—N1	103.1 (2)	C22—C21—C20	120.8 (6)
O6—Mn1—N1	148.9 (2)	C22—C21—C24	117.3 (7)
O4ⁱⁱ—Mn1—N4	170.2 (2)	C20—C21—C24	121.9 (6)
O1ⁱ—Mn1—N4	94.20 (18)	C21—C22—C23	120.6 (7)
O6—Mn1—N4	87.09 (19)	C21—C22—H22	119.7
N1—Mn1—N4	73.34 (19)	C23—C22—H22	119.7
O4ⁱⁱ—Mn1—O5	81.46 (17)	C14—C23—C22	122.0 (7)
O1ⁱ—Mn1—O5	159.11 (18)	C14—C23—H23	119.0
O6—Mn1—O5	57.90 (17)	C22—C23—H23	119.0
N1—Mn1—O5	97.75 (18)	O8—C24—O7	121.9 (6)
N4—Mn1—O5	91.31 (17)	O8—C24—C21	120.3 (7)
O2—Mn2—O3ⁱⁱⁱ	94.0 (2)	O7—C24—C21	117.8 (7)
O2—Mn2—O7	95.2 (2)	O8—C24—Mn2	65.0 (4)
O3ⁱⁱⁱ—Mn2—O7	107.4 (2)	O7—C24—Mn2	56.9 (4)
O2—Mn2—N5	102.3 (2)	C21—C24—Mn2	174.7 (5)
O3ⁱⁱⁱ—Mn2—N5	103.1 (2)	N1—C25—C26	123.6 (6)
O7—Mn2—N5	143.5 (2)	N1—C25—H25	118.2
O2—Mn2—N8	172.5 (2)	C26—C25—H25	118.2
O3ⁱⁱⁱ—Mn2—N8	93.1 (2)	C27—C26—C25	118.9 (7)
O7—Mn2—N8	85.2 (2)	C27—C26—H26	120.6
N5—Mn2—N8	73.5 (2)	C25—C26—H26	120.6
O2—Mn2—O8	82.28 (18)	C26—C27—C28	119.6 (7)
O3ⁱⁱⁱ—Mn2—O8	163.32 (19)	C26—C27—H27	120.2
O7—Mn2—O8	57.07 (18)	C28—C27—H27	120.2
N5—Mn2—O8	93.55 (19)	C29—C28—C27	117.6 (6)
N8—Mn2—O8	91.70 (19)	C29—C28—C30	118.0 (6)
C11—O1—Mn1^v	127.7 (5)	C27—C28—C30	124.3 (6)
C11—O2—Mn2	128.6 (5)	N1—C29—C28	122.9 (6)
C12—O3—Mn2^vi	129.6 (5)	N1—C29—C40	117.3 (6)
C12—O4—Mn1^iv	128.5 (4)	C28—C29—C40	119.8 (5)
C13—O5—Mn1	83.7 (4)	C38—C30—N2	110.4 (5)
C13—O6—Mn1	95.8 (4)	C38—C30—C28	120.7 (6)
C24—O7—Mn2	94.4 (4)	N2—C30—C28	128.9 (6)
C24—O8—Mn2	86.6 (4)	N2—C31—N3	111.7 (6)
C25—N1—C29	117.5 (6)	N2—C31—C32	124.3 (6)
C25—N1—Mn1	126.0 (4)	N3—C31—C32	123.8 (6)
C29—N1—Mn1	116.5 (4)	C37—C32—C33	118.5 (6)
C31—N2—C30	105.4 (5)	C37—C32—C31	123.1 (7)
C31—N3—C38	107.0 (5)	C33—C32—C31	118.5 (6)
C31—N3—H3N	126.5	C34—C33—C32	120.4 (7)
C38—N3—H3N	126.5	C34—C33—H33	119.8
C43—N4—C40	119.2 (5)	C32—C33—H33	119.8
C43—N4—Mn1	124.8 (4)	C33—C34—C35	121.3 (8)
C40—N4—Mn1	115.9 (4)	C33—C34—H34	119.3
C44—N5—C48	118.7 (7)	C35—C34—H34	119.3
C44—N5—Mn2	125.3 (5)	C34—C35—C36	118.4 (7)
C48—N5—Mn2	116.0 (5)	C34—C35—H35	120.8
C50—N6—C49	105.2 (6)	C36—C35—H35	120.8
C57—N7—C50	106.7 (6)	C37—C36—C35	120.8 (7)
C57—N7—H7N	126.7	C37—C36—H36	119.6
C50—N7—H7N	126.7	C35—C36—H36	119.6
C62—N8—C59	118.0 (6)	C36—C37—C32	120.6 (7)
C62—N8—Mn2	125.3 (5)	C36—C37—H37	119.7
C59—N8—Mn2	116.5 (4)	C32—C37—H37	119.7
C2—C1—C6	120.0	C30—C38—N3	105.5 (5)
C2—C1—C11	119.5 (5)	C30—C38—C39	123.4 (6)
C6—C1—C11	120.5 (5)	N3—C38—C39	131.0 (6)
C1—C2—C3	120.0	C40—C39—C38	116.2 (6)
C1—C2—H2	120.0	C40—C39—C41	117.8 (6)
C3—C2—H2	120.0	C38—C39—C41	125.9 (6)
C4—C3—C2	120.0	N4—C40—C39	121.4 (6)
C4—C3—H3	120.0	N4—C40—C29	116.9 (5)
C2—C3—H3	120.0	C39—C40—C29	121.8 (6)
C3—C4—C5	120.0	C42—C41—C39	119.7 (6)
C3—C4—C12	117.1 (5)	C42—C41—H41	120.1
C5—C4—C12	122.6 (5)	C39—C41—H41	120.1
C6—C5—C4	120.0	C41—C42—C43	119.4 (6)
C6—C5—C10	120.0	C41—C42—H42	120.3
C4—C5—C10	120.0	C43—C42—H42	120.3
C7—C6—C5	120.0	N4—C43—C42	122.4 (6)
C7—C6—C1	120.0	N4—C43—H43	118.8
C5—C6—C1	120.0	C42—C43—H43	118.8
C6—C7—C8	120.0	N5—C44—C45	121.8 (7)
C6—C7—H7	120.0	N5—C44—H44	119.1
C8—C7—H7	120.0	C45—C44—H44	119.1
C9—C8—C7	120.0	C46—C45—C44	121.2 (8)
C9—C8—H8	120.0	C46—C45—H45	119.4
C7—C8—H8	120.0	C44—C45—H45	119.4
C8—C9—C10	120.0	C45—C46—C47	118.1 (8)
C8—C9—H9	120.0	C45—C46—H46	120.9
C10—C9—H9	120.0	C47—C46—H46	120.9
C9—C10—C5	120.0	C48—C47—C46	118.1 (7)
C9—C10—H10	120.0	C48—C47—C49	118.2 (6)
C5—C10—H10	120.0	C46—C47—C49	123.7 (7)
C2'—C1'—C6'	120.0	N5—C48—C47	122.1 (6)
C2'—C1'—C11	119.4 (5)	N5—C48—C59	117.4 (6)
C6'—C1'—C11	120.6 (5)	C47—C48—C59	120.4 (6)
C1'—C2'—C3'	120.0	N6—C49—C57	111.1 (6)
C1'—C2'—H2'	120.0	N6—C49—C47	129.0 (7)
C3'—C2'—H2'	120.0	C57—C49—C47	119.9 (6)
C2'—C3'—C4'	120.0	N6—C50—N7	111.9 (6)
C2'—C3'—H3'	120.0	N6—C50—C51	124.6 (7)
C4'—C3'—H3'	120.0	N7—C50—C51	123.3 (6)
C5'—C4'—C3'	120.0	C52—C51—C56	119.3 (7)
C5'—C4'—C12	122.6 (4)	C52—C51—C50	119.0 (7)
C3'—C4'—C12	117.4 (4)	C56—C51—C50	121.7 (7)
C4'—C5'—C6'	120.0	C51—C52—C53	119.8 (8)
C4'—C5'—C10'	120.0	C51—C52—H52	120.1
C6'—C5'—C10'	120.0	C53—C52—H52	120.1
C7'—C6'—C5'	120.0	C54—C53—C52	121.2 (9)
C7'—C6'—C1'	120.0	C54—C53—H53	119.4
C5'—C6'—C1'	120.0	C52—C53—H53	119.4
C8'—C7'—C6'	120.0	C53—C54—C55	119.9 (8)
C8'—C7'—H7'	120.0	C53—C54—H54	120.0
C6'—C7'—H7'	120.0	C55—C54—H54	120.0
C9'—C8'—C7'	120.0	C54—C55—C56	119.2 (8)
C9'—C8'—H8'	120.0	C54—C55—H55	120.4
C7'—C8'—H8'	120.0	C56—C55—H55	120.4
C10'—C9'—C8'	120.0	C51—C56—C55	120.5 (9)
C10'—C9'—H9'	120.0	C51—C56—H56	119.7
C8'—C9'—H9'	120.0	C55—C56—H56	119.7
C9'—C10'—C5'	120.0	N7—C57—C49	105.1 (6)
C9'—C10'—H10'	120.0	N7—C57—C58	130.6 (7)
C5'—C10'—H10'	120.0	C49—C57—C58	124.2 (6)
O2—C11—O1	124.3 (6)	C60—C58—C59	117.5 (7)
O2—C11—C1	117.2 (7)	C60—C58—C57	125.7 (6)
O1—C11—C1	118.5 (7)	C59—C58—C57	116.8 (6)
O2—C11—C1'	114.9 (7)	N8—C59—C58	123.1 (6)
O1—C11—C1'	120.7 (7)	N8—C59—C48	116.4 (6)
O4—C12—O3	125.5 (6)	C58—C59—C48	120.4 (6)
O4—C12—C4'	118.6 (7)	C61—C60—C58	119.6 (7)
O3—C12—C4'	115.8 (7)	C61—C60—H60	120.2
O4—C12—C4	115.2 (7)	C58—C60—H60	120.2
O3—C12—C4	119.2 (8)	C60—C61—C62	118.2 (7)
O6—C13—O5	122.5 (6)	C60—C61—H61	120.9
O6—C13—C14	119.2 (6)	C62—C61—H61	120.9
O5—C13—C14	118.2 (6)	N8—C62—C61	123.5 (8)
O6—C13—Mn1	55.5 (3)	N8—C62—H62	118.2
O5—C13—Mn1	67.1 (4)	C61—C62—H62	118.2
C14—C13—Mn1	174.6 (5)	C63—N9—C64	129.9 (11)
C23—C14—C15	118.5 (6)	C63—N9—C65	109.3 (11)
C23—C14—C13	117.7 (7)	C64—N9—C65	120.8 (10)
C15—C14—C13	123.7 (7)	O9—C63—N9	118.8 (16)
C14—C15—C16	122.5 (6)	O9—C63—H63	120.6
C14—C15—C20	119.6 (6)	N9—C63—H63	120.6
C16—C15—C20	117.9 (6)	N9—C64—H64A	109.5
C17—C16—C15	120.9 (7)	N9—C64—H64B	109.5
C17—C16—H16	119.6	H64A—C64—H64B	109.5
C15—C16—H16	119.6	N9—C64—H64C	109.5
C16—C17—C18	120.4 (8)	H64A—C64—H64C	109.5
C16—C17—H17	119.8	H64B—C64—H64C	109.5
C18—C17—H17	119.8	N9—C65—H65A	109.5
C19—C18—C17	120.8 (8)	N9—C65—H65B	109.5
C19—C18—H18	119.6	H65A—C65—H65B	109.5
C17—C18—H18	119.6	N9—C65—H65C	109.5
C18—C19—C20	121.3 (7)	H65A—C65—H65C	109.5
C18—C19—H19	119.3	H65B—C65—H65C	109.5

O3ⁱⁱⁱ—Mn2—O2—C11	31.4 (8)	C13—C14—C15—C16	1.2 (9)
O7—Mn2—O2—C11	139.3 (8)	C23—C14—C15—C20	−1.1 (9)
N5—Mn2—O2—C11	−73.0 (8)	C13—C14—C15—C20	−177.6 (5)
O8—Mn2—O2—C11	−165.0 (8)	C14—C15—C16—C17	−177.1 (7)
C24—Mn2—O2—C11	167.4 (8)	C20—C15—C16—C17	1.6 (10)
O4ⁱⁱ—Mn1—O5—C13	98.9 (4)	C15—C16—C17—C18	1.2 (12)
O1ⁱ—Mn1—O5—C13	17.7 (6)	C16—C17—C18—C19	−2.9 (13)
O6—Mn1—O5—C13	−1.9 (3)	C17—C18—C19—C20	1.6 (12)
N1—Mn1—O5—C13	−161.1 (3)	C18—C19—C20—C21	−179.7 (7)
N4—Mn1—O5—C13	−87.7 (4)	C18—C19—C20—C15	1.2 (10)
O4ⁱⁱ—Mn1—O6—C13	−75.0 (4)	C14—C15—C20—C19	176.1 (6)
O1ⁱ—Mn1—O6—C13	−171.0 (4)	C16—C15—C20—C19	−2.7 (9)
N1—Mn1—O6—C13	45.1 (5)	C14—C15—C20—C21	−3.1 (8)
N4—Mn1—O6—C13	95.4 (4)	C16—C15—C20—C21	178.1 (6)
O5—Mn1—O6—C13	2.0 (3)	C19—C20—C21—C22	−174.9 (6)
O2—Mn2—O7—C24	78.8 (4)	C15—C20—C21—C22	4.3 (9)
O3ⁱⁱⁱ—Mn2—O7—C24	174.7 (4)	C19—C20—C21—C24	5.1 (9)
N5—Mn2—O7—C24	−39.9 (5)	C15—C20—C21—C24	−175.8 (5)
N8—Mn2—O7—C24	−93.6 (4)	C20—C21—C22—C23	−1.1 (9)
O8—Mn2—O7—C24	1.5 (4)	C24—C21—C22—C23	178.9 (6)
O2—Mn2—O8—C24	−102.9 (4)	C15—C14—C23—C22	4.4 (9)
O3ⁱⁱⁱ—Mn2—O8—C24	−24.9 (8)	C13—C14—C23—C22	−178.9 (6)
O7—Mn2—O8—C24	−1.5 (4)	C21—C22—C23—C14	−3.4 (10)
N5—Mn2—O8—C24	155.2 (4)	Mn2—O8—C24—O7	2.6 (6)
N8—Mn2—O8—C24	81.7 (4)	Mn2—O8—C24—C21	−179.3 (6)
O4ⁱⁱ—Mn1—N1—C25	−8.7 (6)	Mn2—O7—C24—O8	−2.9 (7)
O1ⁱ—Mn1—N1—C25	89.0 (6)	Mn2—O7—C24—C21	179.0 (5)
O6—Mn1—N1—C25	−127.2 (6)	C22—C21—C24—O8	−146.0 (6)
N4—Mn1—N1—C25	179.5 (6)	C20—C21—C24—O8	34.0 (9)
O5—Mn1—N1—C25	−91.4 (6)	C22—C21—C24—O7	32.2 (9)
C13—Mn1—N1—C25	−102.6 (6)	C20—C21—C24—O7	−147.8 (6)
O4ⁱⁱ—Mn1—N1—C29	173.2 (4)	C29—N1—C25—C26	−2.0 (10)
O1ⁱ—Mn1—N1—C29	−89.1 (5)	Mn1—N1—C25—C26	179.9 (6)
O6—Mn1—N1—C29	54.7 (6)	N1—C25—C26—C27	1.7 (12)
N4—Mn1—N1—C29	1.4 (4)	C25—C26—C27—C28	0.0 (12)
O5—Mn1—N1—C29	90.5 (5)	C26—C27—C28—C29	−1.2 (11)
C13—Mn1—N1—C29	79.3 (5)	C26—C27—C28—C30	179.8 (7)
O1ⁱ—Mn1—N4—C43	−77.6 (6)	C25—N1—C29—C28	0.7 (10)
O6—Mn1—N4—C43	24.5 (5)	Mn1—N1—C29—C28	178.9 (5)
N1—Mn1—N4—C43	180.0 (6)	C25—N1—C29—C40	−179.1 (6)
O5—Mn1—N4—C43	82.3 (5)	Mn1—N1—C29—C40	−0.8 (7)
C13—Mn1—N4—C43	53.1 (6)	C27—C28—C29—N1	0.9 (10)
O1ⁱ—Mn1—N4—C40	100.5 (5)	C30—C28—C29—N1	180.0 (6)
O6—Mn1—N4—C40	−157.4 (5)	C27—C28—C29—C40	−179.4 (6)
N1—Mn1—N4—C40	−1.9 (4)	C30—C28—C29—C40	−0.3 (10)
O5—Mn1—N4—C40	−99.6 (5)	C31—N2—C30—C38	−0.3 (8)
C13—Mn1—N4—C40	−128.8 (5)	C31—N2—C30—C28	179.8 (7)
O2—Mn2—N5—C44	5.6 (7)	C29—C28—C30—C38	1.5 (10)
O3ⁱⁱⁱ—Mn2—N5—C44	−91.5 (6)	C27—C28—C30—C38	−179.5 (7)
O7—Mn2—N5—C44	122.3 (6)	C29—C28—C30—N2	−178.6 (7)
N8—Mn2—N5—C44	179.2 (7)	C27—C28—C30—N2	0.4 (12)
O8—Mn2—N5—C44	88.5 (6)	C30—N2—C31—N3	0.3 (8)
C24—Mn2—N5—C44	101.7 (6)	C30—N2—C31—C32	−176.1 (7)
O2—Mn2—N5—C48	−172.7 (5)	C38—N3—C31—N2	−0.1 (8)
O3ⁱⁱⁱ—Mn2—N5—C48	90.2 (5)	C38—N3—C31—C32	176.3 (7)
O7—Mn2—N5—C48	−56.0 (6)	N2—C31—C32—C37	172.2 (7)
N8—Mn2—N5—C48	0.9 (5)	N3—C31—C32—C37	−3.8 (11)
O8—Mn2—N5—C48	−89.9 (5)	N2—C31—C32—C33	−6.2 (11)
C24—Mn2—N5—C48	−76.7 (5)	N3—C31—C32—C33	177.8 (7)
O3ⁱⁱⁱ—Mn2—N8—C62	74.5 (6)	C37—C32—C33—C34	−1.3 (11)
O7—Mn2—N8—C62	−32.8 (6)	C31—C32—C33—C34	177.2 (7)
N5—Mn2—N8—C62	177.3 (7)	C32—C33—C34—C35	1.5 (13)
O8—Mn2—N8—C62	−89.5 (6)	C33—C34—C35—C36	−0.3 (13)
C24—Mn2—N8—C62	−61.4 (6)	C34—C35—C36—C37	−1.0 (12)
O3ⁱⁱⁱ—Mn2—N8—C59	−100.8 (5)	C35—C36—C37—C32	1.2 (12)
O7—Mn2—N8—C59	152.0 (5)	C33—C32—C37—C36	−0.1 (11)
N5—Mn2—N8—C59	2.0 (5)	C31—C32—C37—C36	−178.5 (7)
O8—Mn2—N8—C59	95.2 (5)	N2—C30—C38—N3	0.3 (8)
C24—Mn2—N8—C59	123.4 (5)	C28—C30—C38—N3	−179.8 (6)
C6—C1—C2—C3	0.0	N2—C30—C38—C39	179.0 (6)
C11—C1—C2—C3	−179.8 (9)	C28—C30—C38—C39	−1.1 (11)
C1—C2—C3—C4	0.0	C31—N3—C38—C30	−0.1 (7)
C2—C3—C4—C5	0.0	C31—N3—C38—C39	−178.7 (7)
C2—C3—C4—C12	−173.3 (9)	C30—C38—C39—C40	−0.7 (10)
C3—C4—C5—C6	0.0	N3—C38—C39—C40	177.7 (7)
C12—C4—C5—C6	172.9 (10)	C30—C38—C39—C41	−177.5 (7)
C3—C4—C5—C10	180.0	N3—C38—C39—C41	0.9 (12)
C12—C4—C5—C10	−7.1 (10)	C43—N4—C40—C39	1.2 (10)
C4—C5—C6—C7	180.0	Mn1—N4—C40—C39	−177.0 (5)
C10—C5—C6—C7	0.0	C43—N4—C40—C29	−179.6 (6)
C4—C5—C6—C1	0.0	Mn1—N4—C40—C29	2.2 (7)
C10—C5—C6—C1	180.0	C38—C39—C40—N4	−178.9 (6)
C2—C1—C6—C7	180.0	C41—C39—C40—N4	−1.8 (10)
C11—C1—C6—C7	−0.2 (9)	C38—C39—C40—C29	1.9 (9)
C2—C1—C6—C5	0.0	C41—C39—C40—C29	179.0 (6)
C11—C1—C6—C5	179.8 (9)	N1—C29—C40—N4	−1.0 (9)
C5—C6—C7—C8	0.0	C28—C29—C40—N4	179.3 (6)
C1—C6—C7—C8	180.0	N1—C29—C40—C39	178.2 (6)
C6—C7—C8—C9	0.0	C28—C29—C40—C39	−1.5 (10)
C7—C8—C9—C10	0.0	C40—C39—C41—C42	2.1 (10)
C8—C9—C10—C5	0.0	C38—C39—C41—C42	178.9 (7)
C6—C5—C10—C9	0.0	C39—C41—C42—C43	−1.9 (11)
C4—C5—C10—C9	180.0	C40—N4—C43—C42	−0.9 (10)
C6'—C1'—C2'—C3'	0.0	Mn1—N4—C43—C42	177.1 (5)
C11—C1'—C2'—C3'	176.5 (9)	C41—C42—C43—N4	1.3 (12)
C1'—C2'—C3'—C4'	0.0	C48—N5—C44—C45	0.8 (12)
C2'—C3'—C4'—C5'	0.0	Mn2—N5—C44—C45	−177.5 (7)
C2'—C3'—C4'—C12	−177.1 (8)	N5—C44—C45—C46	−2.2 (15)
C3'—C4'—C5'—C6'	0.0	C44—C45—C46—C47	1.9 (15)
C12—C4'—C5'—C6'	176.9 (8)	C45—C46—C47—C48	−0.5 (12)
C3'—C4'—C5'—C10'	180.0	C45—C46—C47—C49	−178.7 (8)
C12—C4'—C5'—C10'	−3.1 (8)	C44—N5—C48—C47	0.7 (10)
C4'—C5'—C6'—C7'	180.0	Mn2—N5—C48—C47	179.1 (5)
C10'—C5'—C6'—C7'	0.0	C44—N5—C48—C59	178.1 (6)
C4'—C5'—C6'—C1'	0.0	Mn2—N5—C48—C59	−3.4 (7)
C10'—C5'—C6'—C1'	180.0	C46—C47—C48—N5	−0.8 (11)
C2'—C1'—C6'—C7'	180.0	C49—C47—C48—N5	177.5 (6)
C11—C1'—C6'—C7'	3.6 (9)	C46—C47—C48—C59	−178.2 (7)
C2'—C1'—C6'—C5'	0.0	C49—C47—C48—C59	0.1 (10)
C11—C1'—C6'—C5'	−176.4 (9)	C50—N6—C49—C57	−0.9 (8)
C5'—C6'—C7'—C8'	0.0	C50—N6—C49—C47	−178.9 (7)
C1'—C6'—C7'—C8'	180.0	C48—C47—C49—N6	175.6 (7)
C6'—C7'—C8'—C9'	0.0	C46—C47—C49—N6	−6.2 (13)
C7'—C8'—C9'—C10'	0.0	C48—C47—C49—C57	−2.2 (10)
C8'—C9'—C10'—C5'	0.0	C46—C47—C49—C57	176.0 (7)
C4'—C5'—C10'—C9'	180.0	C49—N6—C50—N7	0.9 (8)
C6'—C5'—C10'—C9'	0.0	C49—N6—C50—C51	176.8 (7)
Mn2—O2—C11—O1	25.4 (13)	C57—N7—C50—N6	−0.6 (8)
Mn2—O2—C11—C1	−153.6 (6)	C57—N7—C50—C51	−176.5 (7)
Mn2—O2—C11—C1'	−158.4 (6)	N6—C50—C51—C52	5.0 (12)
Mn1^v—O1—C11—O2	−116.3 (8)	N7—C50—C51—C52	−179.6 (7)
Mn1^v—O1—C11—C1	62.7 (9)	N6—C50—C51—C56	−172.3 (7)
Mn1^v—O1—C11—C1'	67.7 (9)	N7—C50—C51—C56	3.1 (12)
C2—C1—C11—O2	−128.5 (7)	C56—C51—C52—C53	1.0 (14)
C6—C1—C11—O2	51.7 (11)	C50—C51—C52—C53	−176.3 (8)
C2—C1—C11—O1	52.5 (9)	C51—C52—C53—C54	−2.7 (16)
C6—C1—C11—O1	−127.3 (7)	C52—C53—C54—C55	1.8 (17)
C2—C1—C11—C1'	−66 (7)	C53—C54—C55—C56	0.7 (16)
C6—C1—C11—C1'	114 (7)	C52—C51—C56—C55	1.5 (13)
C2'—C1'—C11—O2	59.2 (9)	C50—C51—C56—C55	178.7 (8)
C6'—C1'—C11—O2	−124.4 (8)	C54—C55—C56—C51	−2.4 (14)
C2'—C1'—C11—O1	−124.4 (7)	C50—N7—C57—C49	0.0 (7)
C6'—C1'—C11—O1	52.0 (11)	C50—N7—C57—C58	176.6 (7)
C2'—C1'—C11—C1	−60 (7)	N6—C49—C57—N7	0.6 (8)
C6'—C1'—C11—C1	116 (7)	C47—C49—C57—N7	178.8 (6)
Mn1^iv—O4—C12—O3	−27.7 (11)	N6—C49—C57—C58	−176.3 (7)
Mn1^iv—O4—C12—C4'	148.4 (6)	C47—C49—C57—C58	1.9 (11)
Mn1^iv—O4—C12—C4	156.8 (6)	N7—C57—C58—C60	2.2 (13)
Mn2^vi—O3—C12—O4	114.4 (8)	C49—C57—C58—C60	178.2 (7)
Mn2^vi—O3—C12—C4'	−61.8 (8)	N7—C57—C58—C59	−175.3 (7)
Mn2^vi—O3—C12—C4	−70.3 (9)	C49—C57—C58—C59	0.7 (11)
C5'—C4'—C12—O4	−53.8 (10)	C62—N8—C59—C58	0.3 (10)
C3'—C4'—C12—O4	123.1 (6)	Mn2—N8—C59—C58	175.9 (5)
C5'—C4'—C12—O3	122.6 (7)	C62—N8—C59—C48	180.0 (6)
C3'—C4'—C12—O3	−60.4 (7)	Mn2—N8—C59—C48	−4.4 (8)
C5'—C4'—C12—C4	−121 (5)	C60—C58—C59—N8	−0.9 (11)
C3'—C4'—C12—C4	56 (4)	C57—C58—C59—N8	176.9 (6)
C3—C4—C12—O4	−58.9 (8)	C60—C58—C59—C48	179.5 (7)
C5—C4—C12—O4	128.0 (7)	C57—C58—C59—C48	−2.8 (10)
C3—C4—C12—O3	125.4 (6)	N5—C48—C59—N8	5.3 (9)
C5—C4—C12—O3	−47.7 (11)	C47—C48—C59—N8	−177.2 (6)
C3—C4—C12—C4'	58 (4)	N5—C48—C59—C58	−175.0 (6)
C5—C4—C12—C4'	−116 (5)	C47—C48—C59—C58	2.4 (10)
Mn1—O6—C13—O5	−3.8 (7)	C59—C58—C60—C61	1.3 (12)
Mn1—O6—C13—C14	179.5 (5)	C57—C58—C60—C61	−176.2 (8)
Mn1—O5—C13—O6	3.4 (6)	C58—C60—C61—C62	−1.2 (13)
Mn1—O5—C13—C14	−179.9 (5)	C59—N8—C62—C61	−0.2 (12)
O6—C13—C14—C23	151.0 (6)	Mn2—N8—C62—C61	−175.3 (6)
O5—C13—C14—C23	−25.9 (8)	C60—C61—C62—N8	0.6 (13)
O6—C13—C14—C15	−32.5 (9)	C64—N9—C63—O9	−0.3 (4)
O5—C13—C14—C15	150.6 (6)	C65—N9—C63—O9	−179.8 (13)
C23—C14—C15—C16	177.6 (6)

Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) x−1, y−1, z; (v) x, y−1, z; (vi) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Mn₂(C₁₂H₆O₄)₂(C₁₉H₁₂N₄)₂]·C₃H₇NO
M_r	1203.96
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.240 (2), 14.852 (5), 21.921 (5)
α, β, γ (°)	105.72 (1), 100.48 (1), 101.67 (1)
V (Å³)	2745.0 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.26 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.760, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	21501, 9443, 4800
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.262, 1.06
No. of reflections	9443
No. of parameters	810
No. of restraints	158
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.74, −0.48

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2008).

Selected bond lengths (Å) top

Mn1—O1ⁱ	2.115 (5)	Mn2—O2	2.107 (5)
Mn1—O4ⁱⁱ	2.105 (4)	Mn2—O3ⁱⁱⁱ	2.112 (5)
Mn1—O5	2.431 (5)	Mn2—O7	2.208 (5)
Mn1—O6	2.171 (5)	Mn2—O8	2.384 (5)
Mn1—N1	2.232 (5)	Mn2—N5	2.252 (6)
Mn1—N4	2.259 (5)	Mn2—N8	2.277 (5)

Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1, y, z.

Acknowledgements

We thank the Natural Science Foundation of Jilin Province (No. 20060516), the Doctoral Foundation of Jilin Normal University (No. 2006006), the Science and Technology Institute Foundation of Siping City (No. 2005016), the Subject and Base Construction Foundation of Jilin Normal University (No. 2006041), and the University of Malaya for supporting this work.

References

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